Although Riley never married, he was not immune to the passions of the heart. From 1877 to 1885 there were liaisons with a number of women. In 1877 Riley was engaged to Kate "Kit" Meyers whom he had met through his employment at the Anderson Democrat. The affair ended with the exposure of the Leonainie hoax and Riley's discharge from the Democrat. The following year Clara Bottsford, a school teacher and aspiring poetess, came to Greenfield and roomed at the Riley family home. Her relationship with the Poet began shortly thereafter and in 1880 they became engaged. The affair lasted for five tumultuous years with Clara's reputation evolving into that of Riley's mistress. Riley ended the relationship in 1885. Clara, with her reputation in tatters, lost her job at the Indianapolis Herald and finally married a tavern keeper, who later abandoned her.
Prior to 1880 Riley was corresponding with Elizabeth "Lizzie" Kahle Brunn of Pennsylvania. Judging from the correspondence which dates from 1879 to 1884 the two never met, although Riley's platform schedule did take him close to Lizzie's home. The correspondence begins to dwindle after 1882 and ends when Lizzie married Harry Brunn. The Poet was also writing to Eda Brown, the wife of James McClanahan his friend from the medicine show days. The two became involved during one of McClanahan's absences and the affair ended upon his return.
In 1880 Riley was spending time with Grace Monk Morland, a variety show singer
and dancer at an Indianapolis theatre. He was also corresponding with Ella Wheeler
Wilcox, whom he termed "the Golden Girl." Like Riley, Ella was a popular poet, who
lived in Milwaukee. Riley met her during his platform tour. She was his ideal
woman and was the inspiration for the poem "Her Beautiful Hands."